Synthesis of Sulfur‐Substituted α‐Stereogenic Amides and Ketones:
- TCHLab
- Oct 10, 2011
- 1 min read
Highly enantioselective Sulfa-Michael Addition (SMA) of 1,4-dicarbonyl but-2-enes
Fangli Zhao, Wen Zhang, Yuanyong Yang, Yuanhang Pan, Wenchao Chen, Hongjun Liu, Lin Yan, Choon‐Hong Tan and Zhiyong Jiang
Advanced Synthesis and Catalysis, 2011, 353, 2624 – 2630
Abstract: Conjugate addition to 1,4‐dicarbonylbut‐2‐enes will generate an α‐stereogenic center with respect to one of the carbonyl groups, which informally, can be considered as an inversion of normal reactivity patterns or umpolung protocol. In this paper, the addition of tert‐butyl mercaptan to 1,4‐dicarbonylbut‐2‐enes including (E)‐4‐oxo‐4‐arylbutenamides and (E)‐4‐oxo‐4‐arylbutenones has been developed, to synthesize a series of chiral sulfur‐substituted α‐stereogenic amides and ketones in high regioselectivity and enantioselectivity (up to 98% ee).
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